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Topic: Methylone synthesis (Read 6993 times)

Chicken

Do any bees know where a synthesis might be found for methylone, 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one. There are some journal entries regarding it's effects which are, in thses articles it states that the methylone was synthed, but does not indicate what the synthesis proceedure is. There alslo are several reports for usage on erowid at

Rhodium

I have never heard of the reaction (which essentially is a FC acylation with PPA as the lewis acid) being used with formic acid. There is nothing that would stop any formed piperonal from acylating unreacted benzodioxole, so I guess your suggestion would be a dead end...

Antoncho

1st, as for HCOOH formylations - Primo, believe me, this IS a dead end, i've done once quite a thorough search on this and found nihil - there was one exciting article that Lugh sent me, but it turned out pretty discouraging as well.

2nd, AFAIK, there's no specific need to use NBS for brominating 'propiopiperone' , dioxane*Br2 should work as well.

PrimoPyro

Since The epoxide opens to give the more stable carbocation, and the amine attaches to the most stable carbocation, I would think the amine would be in the benzyl position, with the alcohol being at the isopropyl position.

PrimoPyroWill perform sexual favors for females in exchange for 1,2-dimethylaziridine. PM for details.

A typical experimental procedure for the microwave-promoted synthesis of benzophenones is exemplified by the following example:

3,4-Dimethoxy-4-methyl-benzophenone (Run 1): Polyphosphoric acid (15 g) was added to veratrole (1.0 g, 7.25 mmo1) and p-toluic acid (1.08 g, 7.97 mmo1) in an open 50 mL round bottom flask equipped with a magnetic stirring bar. The mixture was placed in the cavity of the microwave oven and irradiated at 100% power for 45 s, with the maximum allowed temperature set at 120 deg C. The resulting deep red mixture was allowed to cool, and then poured onto ice/water (100 mL). The precipitate was filtered off, washed with water and dried in air. Recrystallisation (iPrOH) afforded the product as beige crystals, 1.52 g, (82%) of m.p. 127-128 deg C.

AbstractIn the past 35 years, a wide variety of illicit drugs have appeared in the clandestine market. Many of these compounds are based on the structure of amphetamine (1-phenyl-2-aminopropane) to which various functional or structural groups have been added. Previous modifications to the amphetamine molecule include addition of a methylenedioxy bridge to give 3,4-methylenedioxyamphetamine, and attachment of alpha,beta-keto oxygen to yield cathinone. A chemical synthesis integrating the salient functional/structural groups of these two classes of amphetamine analogs results in manufacture of methylenedioxycathinone (MDCATH). In each instance, N-alkylation of these analogs provides a series of homologs. Furthermore, many of these analogs/homologs meet several criteria which typically support the clandestine laboratory synthesis of novel illicit drugs (`designer drugs'). The MDCATH analogs represent a potentially new series of `designer drugs' whose chemical characteristics have not previously been reported. Appropriate selection of analytical, chemical and physical tests will enable rapid identification of these analogs by a comparative analysis using the data provided.

AbstractStructurally, methcathinone is to cathinone what methamphetamine is to amphetamine. Due to increased interest in the abuse of suck agents we wished to determine if certain derivatives of cathinone would behave in a manner consistent with what is known about their amphetamine counterparts; that is, can amphetamine structure-activity relationships be extrapolated to cathinone analogs? As expected on the basis of known structure-activity relationships for amphetaminergic agents, both N-monoethylcathinone and N-mono-n-propylcathinone (N-Et CAT and N-Pr CAT; ED50 = 0.77 and 2.03 mg/kg, respectively) produced amphetamine-like stimulus effects in rats trained to discriminate 1 mg/kg of (+)amphetamine from Vehicle and were somewhat less potent than racemic methcathinone. In contrast, (-)N,N-dimethylcathinone or (-)Di Me CAT (ED50 = 0.44 mg/kg) was more potent than expected; although (+)N,N-dimethylamphetamine is sevenfold less potent than (+)methamphetamine, (-)Di Me CAT is only about 1.6-fold less potent than (-)methcathinone, and is essentially equipotent with (-)cathinone. In addition, although it has been previously demonstrated that 1-(3,4-methylenedioxyphenyl) -2-aminopropane (MD A) results in stimulus generalization in rats trained to discriminate (+)amphetamine or DOM from vehicle; the cathinone counterpart of MDA (i.e., MDC) resulted in partial (maximum: 58%) generalization in (+)amphetamine-trained animals, and failed to produce >7% DOM-appropriate responding in rats trained to discriminate DOM from vehicle. On the other hand, the N-methyl analog of MDC (i.e., MDMC) behaved in a manner similar to that of the N-methyl analog of MDA (i.e., MDMA); that is, st (+)amphetamine stimulus (MDMC: ED50 = 2.36 mg/kg) but not a DOM stimulus generalized to MDMC. In MDMA-trained rats, stimulus generalization occurred both to MDC and MDMC (ED50 = 1.64 and 1.60 mg/kg, respectively). Although this and previous studies have demonstrated that significant parallelisms exist between the structure-activity relationships of amphetamine analogs and cathinone analogs, we now report several unexpected qualitative and/or quantitative differences. It is suggested that caution be used in attempting to draw conclusions or make predictions about the activity and potency of novel cathinone analogs by analogy to the structure-activity relationships derived from amphetamine-related agents; it would appear that each new cathinone analog will require individual investigation.

AbstractA simple method for the preparation of homochiral ring-substituted 1-aryl-2-aminopropanones 2 (`cathinones´) is described, involving initial Friedel–Crafts acylation of aromatics with (S)- or (R)-N-trifluoroacetylalanyl chloride, followed by acid hydrolysis of the intermediate trifluoroacetamido intermediates 1, for which X-ray diffraction analysis confirmed the structures.

(S)-N-Trifluoroacetylalanine

1,1,3,3-Tetramethylguanidine (3.75 mL, 30 mmol) was added to a suspension of L-alanine (2.0 g, 22 mmol) in MeOH (11 mL). After 5 min, ethyl trifluoroacetate (3.3 mL, 28 mmol) was added and the reaction was stirred for 4 h at room temperature. The solvent was then removed by rotary evaporation and the residue dissolved in H2O (35 ml) and acidified with concentrated HCl (4 mL). After stirring for 15 min, the mixture was extracted with EtOAc (2×30 mL) and the organic layers were combined and washed with brine (30 mL), dried over Na2SO4 and rotary evaporated to give a solid which was washed with n-hexane and dried to afford the crude amide, mp 62–64°C, yield 3.5 g (86%), sufficiently pure for all subsequent uses.

General procedure for the preparation of (S)-2-trifluoroacetamido-1-aryl-1-propanones 1

To a stirred suspension of (S)-N-trifluoroacetylalanine (1 g, 5.4 mmol) in dry CH2Cl2 (20 mL), cooled to 0°C in an ice-water bath, was added oxalyl chloride (1.1 mL, 12.8 mmol) followed by pyridine (1 drop). The reaction mixture was allowed to warm gradually to room temperature and was then stirred further for 5 h. The solvent and excess oxalyl chloride were removed by rotary evaporation at 35°C to afford the crude acid chloride. To this chloride was then added with stirring a solution of the aromatic compound (5.4 mmol) in CH2Cl2 (5 mL), followed by AlCl3 (0.72 g, 5.4 mmol) and the resulting mixture was allowed to react for 18 h. The reaction mixture was then cooled in an ice-water bath and slowly quenched with 1N HCl (30 mL) and CH2Cl2 (30 mL). The aqueous layer was extracted with CH2Cl2 (2×30 mL) and the organic layers were combined, dried over Na2SO4, and rotary evaporated to give the crude product 1, which was crystallized in hexane.

General procedure for the preparation of (S)-2-amino-1-aryl-1-propanone hydrochlorides 2

The (S)-2-trifluoroacetamido-1-aryl-1-propanone derivatives 1 (0.7 mmol) were dissolved in 2-propanol (16 mL) and concentrated HCl (12 mL). The resulting solutions were then stirred at 40°C for 12 h. Elimination of the solvent by rotary evaporation, followed by addition of diethyl ether (15 mL) and 2-propanol (0.5 mL) precipitated the hydrochloride salts 2.

Abstract?-N-Acylamino acids have been developed as useful reagents for the preparation of optically pure ?-aminoalkyl aryl ketones. Protection of the amino group as either the ethoxycarbonyl or benzenesulfonyl derivative allows alanine to serve as an effective educt for the chirally specific synthesis of a variety of structures containing the phenylethylamine backbone. Benzene undergoes Friedel-Crafts acylation with the N-acylalanine acid chloride? Catalyst complexation with oxygenated aromatics, however, prohibits acylation of aryl ethers. An arylmetallo reaction scheme overcomes this problem and also affords regiospecificity not attainable in conventional acylations. As examples, optically pure ephedrines and amphetamines were directly synthesized without recourse to resolution since the chirality of the amino acid educt was entirely conserved throughout the process.

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somuchclass

I have tried methylone (MDMCAT) for myself; in fact, I did a total of 6 grams of it, and I have heard of someone at the hive mentioning having intoxicating himself on MDCAT, but does anyone here have any information or personal experience with the N-ethyl homologue of methylone, MDECAT?